Imidazole → Dechloroclotrimazole

HRID 429764노트

반응식

HRID 429764 반응식
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].[C:8]1([C:14](Cl)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CN(C=O)C>[C:14]([N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 6456Trityl chlorideHCID 24758Sodium hydride

생성물 1

HCID 618231Dechloroclotrimazole수율 83%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Imidazole (10.0 g, 146.9 mmol) was added to sodium hydride (60% dispersion in mineral oil, pre-washed in hexane, 6.5 g, 161.6 mmol) in DMF (200 ml), triphenylmethylchloride (41.0 g, 146.9 mmol) was then added and the reaction mixture stirred at room temperature for 18 h. The mixture was poured onto ice and the solid precipitate formed filtered off and partitioned between water and dichloromethane. The organic phase was washed with brine and dried over sodium sulphate and concentrated in vacuo to give the title compound (37.8 g, 83%). 1H NMR (CDCl3) δ 7.42-7.03 (1H, m). MS (ES) m/e 311 [M+H]+.

후처리

  1. additionwas then added
  2. additionThe mixture was poured onto ice
  3. customthe solid precipitate formed
  4. filtrationfiltered off
  5. custompartitioned between water and dichloromethane
  6. washThe organic phase was washed with brine
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-934d32079b2e43a4ba965bf8df977f30
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06319922B1

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